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Middlebury Vacation Rentals

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Vacation Rentals in Middlebury

Downtown Middlebury 3 Bedroom Home - Walk Everywhere!

Downtown Middlebury 3 Bedroom Home - Walk Everywhere!

Middlebury, VT

Located in the heart of Middlebury, this apartment building is within a 15-minute walk of National Museum of the Morgan Horse and Middlebury College. Town Hall ...

4.8/5Exceptional! (8 reviews)
Great location!

"Great location and perfect place for relaxing a few days—or more—in this beautiful town."…"

Reviewed on Aug. 30, 2020

Downtown Middlebury 3 Bedroom Home - Walk Everywhere!
Walk Everywhere in Middlebury

Walk Everywhere in Middlebury

60 Monroe Street, Middlebury, VT

Situated in Middlebury, this historic holiday home is within 1 mile (2 km) of Town Hall Theater and Middlebury College. Vermont Folklife Center and National ...

5/5Exceptional! (23 reviews)
Fabulous House

"This house was extremely comfortable with its open floor plan for our family of 7 who were in Middlebury for an intimate wedding. We are close to downtown and all the wedding events. The large deck and fire pit were an added bonus each evening. This property was perfect for us."…"

Reviewed on Sep. 27, 2020

Walk Everywhere in Middlebury
Downtown Home in Historic Middlebury

Downtown Home in Historic Middlebury

11 Elm St, Middlebury, VT

Situated in Middlebury, this historic holiday home is within 1 mile (2 km) of National Museum of the Morgan Horse and Middlebury College. Town Hall Theater and ...

5/5Exceptional! (3 reviews)
Charming!!!!!

"The place was absolutely one of the most charming places we have ever stayed. Everything we needed we needed was provided from cookware, to luxury bedding, to very courteous and responsive owners. Speaking of the bedding....we had the most heavenly sleep thanks to the amazing mattresses!!! I cannot ..."…"

Reviewed on Jan. 1, 2020

Downtown Home in Historic Middlebury

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Charming Condo in Resort Community w/ Pools, hot Tub, & Tennis Near Sugarbush!

Charming Condo in Resort Community w/ Pools, hot Tub, & Tennis Near Sugarbush!

202 Bridges Circle, Warren, VT

Located in Warren, this family-friendly condo is 0.6 mi (0.9 km) from Sugarbush Ski Resort, and within 9 mi (15 km) of Mad River Glass Gallery and Artisans' ...

4.8/5Exceptional! (6 reviews)
Sugarbush rental

"Overall a great property with tremendous views of the mountains. Pool was well-maintained. Buildings could use a paint job which I'm sure they have scheduled."…"

Reviewed on Jul. 26, 2019

Charming Condo in Resort Community w/ Pools, hot Tub, & Tennis Near Sugarbush!
Lake George Water Front Cabin Spectacular Views

Lake George Water Front Cabin Spectacular Views

2270 Black Point Rd, Ticonderoga, NY

Located in North Lake George, this historic cabin is within 6 miles (10 km) of Star Trek: Original Series Set Tour, Ticonderoga Heritage Museum and Ticonderoga ...

4.7/5Exceptional! (15 reviews)
Amazing Place and Awesome Host

"The property is built on love and it reflects. It has everything a family needs. Its clean, beautiful and kids (small) friendly. We enjoyed a lot."…"

Reviewed on Oct. 5, 2020

Lake George Water Front Cabin Spectacular Views
Kamp Koby

Kamp Koby

2 out of 5
96 Lhcs Rd, Fair Haven, VT

Situated on a lake, this cabin is 0.1 mi (0.1 km) from Lake Hortonia and within 6 miles (10 km) of Beebe Pond and Half Moon State Park. Halfmoon Pond State Park ...

Kamp Koby
The Knoll~ Lake Front Cabin on Beautiful Lincoln Pond!

The Knoll~ Lake Front Cabin on Beautiful Lincoln Pond!

15 Konis Way, Elizabethtown, NY

This Elizabethtown cabin is on the beach, 9.5 mi (15.3 km) from Lake Champlain, and within 20 mi (32 km) of Roaring Brook Falls and Crown Point State Historic ...

4.9/5Exceptional! (25 reviews)
Just as I had hoped

"The rental was just as described and we enjoyed our stay very much. We were in cabin 1 and had good views of the water from most rooms. We loved the screened in porch, although small it was wonderful. Be sure to visit Split Rock Falls (about 25 minutes away), and kayak across Lincoln Pond to the ..."…"

Reviewed on Sep. 4, 2020

The Knoll~ Lake Front Cabin on Beautiful Lincoln Pond!
Moose Lodge Near Lake George

Moose Lodge Near Lake George

27cottage road, Ticonderoga, NY

Located in North Lake George, this holiday home is within 3 miles (5 km) of Ticonderoga Historical Society, Star Trek: Original Series Set Tour and Ticonderoga ...

4.7/5Exceptional! (20 reviews)
Great Location!

"Everything was great! The house was just as described and we had no issues. We had a great weekend hiking and loved the proximity to the lake."…"

Reviewed on Oct. 12, 2020

Moose Lodge Near Lake George
Private Ski Lodge With Giant Hot Tub Less Than Two Miles to Sugarbush!

Private Ski Lodge With Giant Hot Tub Less Than Two Miles to Sugarbush!

3123 W Hill Rd, Warren, VT

Situated in Warren, this holiday home is within 6 miles (10 km) of Sugarbush Ski Resort, Ole's Cross Country Center and Blueberry Lake Cross Country and Snowshoeing ...

4.9/5Exceptional! (11 reviews)
Awesome Fall Getaway

"We had an amazing time at this house. It is very well maintained and had plenty of room for all 15 of us. Everyone enjoyed the hot tub, too! It would have been nice to have a working TV in the basement but everyone survived. We would definitely go back!"…"

Reviewed on Oct. 14, 2020

Private Ski Lodge With Giant Hot Tub Less Than Two Miles to Sugarbush!
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See all available properties in Middlebury
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlebury. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Middlebury?
Yes, we offer vacation rentals close to the most popular attractions in Middlebury, or you can go with a more remote option if you want a relaxing place to stay. Our travelers say Middlebury has a good selection of restaurants. Make sure you have time to check out the architecture and university setting during your trip.
What’s there to see and do in Middlebury?
Cultural attractions to visit include Town Hall Theater and Kevin P. Mahaney ‘84 Center for the Arts. In the larger area, you’ll find popular places like Sugarbush Ski Resort and Green Mountain National Forest.
What’s a vacation rental in Middlebury like?
Vacation rentals are private properties you can stay in for a couple of days or more in Middlebury. Vacation rentals feature amenities like WiFi and washers and dryers so you’ll have everything you need. If you’re concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You’ll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family trips.

Other types of properties in Middlebury you may be interested in

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
Free cancellationReserve now, pay when you stay
The price is CA $162 per night from Nov 3 to Nov 4
Middlebury Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street, US Rt 7 / Historic Ethan Allen Hwy, Middlebury, VT
Free cancellationReserve now, pay when you stay
The price is CA $182 per night from Nov 2 to Nov 3
Courtyard Middlebury
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.